Bicyclo[2.2.1]hept-2-en-2-ylboronic acid → HCID 68312847, compound

HRID 1472908Notes

Reaction equation

HRID 1472908 reaction equation
C12CC(CC1)C=C2B(O)O.[CH:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][C:12]=1[C:21]1[N:26]=[C:25]([CH2:27][NH:28][C@H:29]([CH:32]([CH3:34])[CH3:33])[CH2:30][OH:31])[C:24]([F:35])=[CH:23][CH:22]=1>[Pd].CC(C)CCO>[F:35][C:24]1[C:25]([CH2:27][NH:28][C@H:29]([CH:32]([CH3:34])[CH3:33])[CH2:30][OH:31])=[N:26][C:21]([CH:12]2[CH2:13][CH2:14][C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:11]2)=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 44119810Bicyclo[2.2.1]hept-2-en-2-ylboronic acidHCID 68312626HCID 68312626, compound

Product 1

HCID 68312847HCID 68312847, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 31260Isoamyl AlcoholSolvent

Procedure

(R)-2-4(6-(3,4-dihydronaphthalen-2-yl)-3-fluoropyridin-2-yl)methyl)amino)-3-methylbutan-1-ol was prepared according to Example 199, substituting 3,4-dihydronaphthalen-2-ylboronic acid for bicyclo[2.2.1]hept-2-en-2-ylboronic acid. (R)-2-(((6-(3,4-dihydronaphthalen-2-yl)-3-fluoropyridin-2-yl)methyl)amino)-3-methylbutan-1-ol was subjected to hydrogenation (H2 atmosphere, Pd/C catalyst) to provide the title compound. MS (ESI+) m/z 343 (M+H)+.

Sources & evidence

ORD record
ord-021f382583734ca592e9bd993b95c73f
Source dataset
uspto-grants-2015_04
Patent number
US09012651B2

Reaction notes

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